Adamantanone → HCID 22948017, compound

HRID 376947Notes

Reaction equation

HRID 376947 reaction equation
[CH3:1][O:2][CH:3]([C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([Cl:20])[CH:13]=1)P(OCC)(=O)OCC.[CH:21]12[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:29][CH:23]([CH2:24]3)[C:22]1=O)[CH2:28]2.C([N-]C(C)C)(C)C.[Li+]>C1COCC1>[Cl:20][C:14]1[CH:13]=[C:12]([C:3]([O:2][CH3:1])=[C:22]2[CH:23]3[CH2:29][CH:27]4[CH2:26][CH:25]([CH2:30][CH:21]2[CH2:28]4)[CH2:24]3)[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=1

Participants

5

Reactant 3

HCID 64151AdamantanoneHCID 2724682Lithium diisopropylamideHCID 15477419HCID 15477419, compound

Product 1

HCID 22948017HCID 22948017, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-68 °C

Procedure

Phosphonoate 8 (4.62 g, 14 mmol) and 2-adamantanone (2.58 g, 17 mmol) were dissolved in anhydrous THF (35 ml) under argon and cooled to -68° C. Dropwise addition of lithium diisopropylamide (18.6 mmol) in anhydrous THF (20 ml) at -68° C. generated the ylid, followed by subsequent olefination of the ketone. The reaction was slowly warmed to room temperature over 2 h and then stirred at 75° C. for 1 h. The solution was partitioned between EtOAc/NH4Cl, dried over Na2SO4, evaporated and purified by silica gel chromatography (2% EtOAc/hexanes), yielding 2.5 g (55%) of enol ether 9 as an oil.

Workup

  1. temperatureThe reaction was slowly warmed to room temperature over 2 h
  2. customThe solution was partitioned between EtOAc/NH4Cl
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. custompurified by silica gel chromatography (2% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dea6b140bf3e44a8b62fa2af96443d03
Source dataset
uspto-grants-2000_02
Patent number
US06022964

Reaction notes

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